


Advice

by ChocolateKid



Category: Supernatural
Genre: Bisexual Dean Winchester, Clueless Sam, Established Relationship, Fluff, M/M, Marriage Proposal, Misunderstandings, Nervous Dean, Oblivious Sam, Oops, Phone Calls & Telephones, Romantic Dean, Secret Relationship, Texting, Wedding Planning, and thinks dean is gonna ask cas out, but not really, dean wants to propose to cas, he calls sam in a frenzy, oh so many misunderstandings, sam didn't know they were even dating
Language: English
Status: Completed
Published: 2017-09-14
Updated: 2017-09-14
Packaged: 2018-12-29 22:12:07
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 845
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12094542
Author URL: https://archiveofourown.org/users/ChocolateKid/pseuds/ChocolateKid
Summary: Dean wants to propose to his boyfriend. He calls Sam for advice.Enter oblivious!Sam.





	Advice

**Author's Note:**

> Wow, I actually managed to write something else. It's short, I know, but I kind of needed some clueless Sam. ;) There aren't enough fics around here...
> 
> Thanks for reading, everybody! Enjoy.

**Dean:** _Sammy. Call me. It's important._

Frowning, Sam looked down on his phone, reading his brother's message a second and then a third time before quickly dialing his number.

If Dean said it was important, it probably was, and since it wasn't like Dean to talk on the phone much anyway, him wanting Sam to call was unusual enough on its own. Sam didn't know what to expect. He hoped it was nothing bad...

Dean picked up after the second ring.

"Hey, Sammy," he said, sounding uneasy, and Sam's face contorted into an even deeper frown. Dean was behaving weirdly. That didn't sound good at all.

"What happened?" Sam asked, not bothering with small talk. He had to know what was going on, and fast.

"Nothing happened," Dean replied, huffing an uncomfortable laugh and it was a sound Sam had never heard leaving his brother's mouth before. "Not yet, at least," he added cryptically.

"Dean, just tell me what's going on, please? I'm starting to get worried..." Sam muttered, wishing for Dean to just get on with it. He was feeling too anxious for patience.

There were a few seconds of silence from the other end of the line. Then, Dean answered, slowly, "I'm... Sammy, I'm-- I'm gonna ask Cas to... you know... tonight."

And this was so not what Sam had expected to hear.

"You're-- Wait, you're finally gonna ask him? That's amazing, Dean!" Sam exclaimed, worry quickly turning into happy surprise. Dean had been crushing on his roommate Castiel since the day they'd met, and it'd been obvious to everyone except them that the feelings were returned. Still, neither of those idiots ever seemed to be able to make a move. Hell, Dean wasn't even officially out of the closet yet -- even though everybody knew, obviously. And all of a sudden, seemingly out of _nowhere_ , Dean had decided to ask Castiel out? This was amazing.

"What brought this on though?" Sam added, curious about Dean's change of heart. Not that he hadn't known it was gonna happen eventually.

"I-- I don't know. I mean, I've been thinking about it for a while and it's just... We were eating dinner a few days ago and I looked at him and he smiled and... suddenly I had this feeling that I had to do something, you know? I mean... it's been _years_ , Sammy," he said, nervous anticipation still in his voice.

"Yeah, tell me about it," Sam laughed, remembering every wistful glance, every lingering touch those two dorks had exchanged over the last six years and wondering exactly how nothing could have happened between them for so long. It had seemed inevitable.

But now they were finally gonna suck it up and get together. Sam was exhilarated.

"But, Sammy..." Dean started quietly, voice unsure and hesitant. "What if-- what if he says no?"

"He won't say no!" Sam exclaimed, louder than intended, but then again the thought of Castiel refusing Dean was so far off his mind it wasn't even a possibility. "Dean, I swear to you, that guy is _head over heels_ for you! He'll say yes. I'm sure of it," he tried to calm Dean down.

"Yeah... Yeah, you might be right," Dean agreed hesitantly, still sounding a little doubtful, but determined to go through with it. Sam felt his heart swell with pride for his bigger brother.

"How should I, you know, go about this?" he then asked. "Do I take him out for dinner or something, or is that too cheesy? Do you think he'll suspect something? Or should I just do it at home? I don't want to pressure him into saying yes by doing it publicly, you know? But wouldn't it be more _romantic_ in a restaurant? Over a glass of wine and with music in the background? Then again, we're not the types to go to fancy restaurants, so what if he'll feel uncomfortable? God, Sammy, I'm losing my mind here!" he complained and Sam couldn't suppress the chuckle. It was kind of hilarious to hear his brother being self-conscious. Sam hadn't even known Dean could ramble like this.

"Dean, you'll be fine," Sam assured him, the smile still in his voice, and he knew if Dean had been next to him right now, he would've put his hand on his shoulder to calm him down. "I don't think it really matters where you go. So just do whatever feels right. I'm sure Cas will say yes either way."

"You really think so?" Dean asked timidly and Sam rolled his eyes in exasperation.

"Yes! Now hang up and prepare your speech, you idiot," Sam laughed and even Dean couldn't help but chuckle slightly.

"Okay, Sammy. Thanks for calling and... everything," he said. "I'll text you when it's over," he promised.

"Sure," Sam said. "Good luck, jerk."

"Thanks, bitch."

* * *

That night Sam received a message.

 **Dean:** _He said yes!!!!_

Sam smiled to himself, about to answer, when another message came through.

 **Dean:** _Oh, and t_ _he wedding will be in June, probably._

 **Sam:** _I knew it!! ...Wait, what wedding?_


End file.
